(R)-2-Amino-1-(3-chlorophenyl)ethanol → 5-(4-{4-[(2R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-piperidin-1-yl}-benzylidene)-2-morpholin-4-yl-thiazol-4-one

HRID 2188298Notes

Reaction equation

HRID 2188298 reaction equation
[N:1]1([C:7]2[S:8][C:9](=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:10](=[O:12])[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)[OH:30]>>[Cl:37][C:33]1[CH:32]=[C:31]([C@@H:29]([OH:30])[CH2:28][NH:27][CH:23]2[CH2:22][CH2:21][N:20]([C:17]3[CH:16]=[CH:15][C:14]([CH:13]=[C:9]4[S:8][C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[N:11][C:10]4=[O:12])=[CH:19][CH:18]=3)[CH2:25][CH2:24]2)[CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanol2×HCID 699211351-[4-(2-morpholin-4-yl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one2×

Product 1

HCID 699226305-(4-{4-[(2R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-piperidin-1-yl}-benzylidene)-2-morpholin-4-yl-thiazol-4-one

Procedure

The title compound was prepared from 1-[4-(2-morpholin-4-yl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one (which was obtained in Intermediate 28) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol (which was obtained in Intermediate 1) according to the procedure of Example 1 as a yellowish solid; mp>70° C. (dec.); 1 H NMR (300 MHz, DMSO-d6) δ1.20-1.40 (m, 2 H), 1.70-1.95 (m, 2 H), 2.60-2.90 (m, 7 H), 3.50-4.00(m, 8 H), 4.55-4.65(m, 1 H), 5.46 (brs, 1 H), 7.02 (d, J=9.0 Hz, 2 H), 7.25-7.45 (m, 7 H), 7.54 (s, 1 H); MS (ES) m/z: 527.1(MH+, 100%); HRMS Calcd. for C27H32CIN4O3S (MH+): 527.1884. Found: 527.1863.

Sources & evidence

ORD record
ord-d42515235d6642f7b58672cbcf86004b
Source dataset
uspto-grants-2002_06
Patent number
US06410734B1

Reaction notes

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